US4790978A - Method for disinfection - Google Patents

Method for disinfection Download PDF

Info

Publication number
US4790978A
US4790978A US06/948,261 US94826186A US4790978A US 4790978 A US4790978 A US 4790978A US 94826186 A US94826186 A US 94826186A US 4790978 A US4790978 A US 4790978A
Authority
US
United States
Prior art keywords
ester compound
process according
chain alkyl
microorganisms
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US06/948,261
Inventor
Stig Allenmark
Magnus Lindstedt
Lars Edebo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Berol AB
Nouryon Surface Chemistry AB
Original Assignee
Berol AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Berol AB filed Critical Berol AB
Assigned to BEROL KEMI AB reassignment BEROL KEMI AB ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ALLENMARK, STIG, EDEBO, LARS, LINDSTEDT, MAGNUS
Application granted granted Critical
Publication of US4790978A publication Critical patent/US4790978A/en
Priority to US07/775,096 priority Critical patent/US5204060A/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Definitions

  • Amphiphilic compounds of the quaternary ammonium type have for a long time been known to exhibit strong antimicrobial activity, the disclosure by Domagk in 1935 having great impact on the development of this field. (G. Domagk, Dtsch. Med. Wienschr. 61, 829 (1935)). It has become evident, however, from studies of acute as well as chronic toxicity, that these compounds may give rise to skin irritation and hypersensitivity, and therefore are not quite recommendable for certain applications.
  • Another object of this invention is to find antimicrobial compounds which do not have the drawback mentioned above.
  • Another object of the invention is to permit a rapid inactivation by a controllable degradation of the antimicrobial compound.
  • Still another object is that the degradation will take place at pH-values from about 6 to about 8.5 which is a pH-value that does not give rise to skin irritation and the like.
  • R I , R II , and R III are hydrogen or lower alkyl groups and R IV is an long chain alkyl group having 10-18 carbon atoms
  • R V is hydrogen or a group having the formula R VI N + H 3 where R VI is an alkylene group having 3-4 carbon atoms
  • A is a monovalent counter ion and n is the number of cationic groups in the ester compound, as a temporary microbicide in an aqueous medium at a pH-vlue from about 6 to about 8.5 for disinfection of products or in products for disinfection to be brought in contact with food, human beings and animals, e.g.
  • the microorganisms are inactivated in an initial phase by exposing the microorganisms in an aqueous medium at a pH-value from about 6 to about 8.5 to the long-chain alkyl ester and the long-chain alkyl ester is detoxicated due to a hydrolytic reactiion which takes place concurrently and subsequently with the inactivation of the microorganisms so that the content of the ester in a short time reaches an innocuous level.
  • the lower alkyl groups R I , R II and R III are preferably alkyl groups having 1-4 carbon atoms and most preferably they are methyl groups.
  • R IV is a straight chain alkyl group.
  • the counter ion A is normally a halide ion, such as chloride, or HSO 4 - . Examples of preferred embodiments are esters having the formulae ##STR3## where R IV and A have the above meanings.
  • ordinary alkyl ester compounds have an extremely slow hydrolysis rate at these pH-values.
  • the charged long chain alkyl esters I exhibit a useful rate of ester hydrolysis in a pH-range from about 6 to about 8.5 and especially in the pH-range from about 7 to about 8 which, in the present invention, is advantageously used in order to obtain an initially complete microbicidal effect while only a limited toxic effect is exerted against human beings and animals.
  • the latter advantage will be more pronounced when longer contact times, e.g. half an hour or more, are had between the disinfected or disinfecting products and human beings and animals.
  • the long-chain alkyl esters are added in such an amount that the effective concentration in the aqueous medium will be at least 2 ppm, preferably between 5 and 200 ppm, even if other concentrations may be used depending on the specific conditions at application.
  • lower alkyl groups in the above formula are methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, and isobutyl, but ethyl and especially methyl are the preferred groups.
  • the long chain alkyl group R IV can be decanyl, dodecanyl, dodecenyl, tetradecanyl, hexadecanyl, octadecanyl, octadecenyl, octadecandienyl, and octadecantrietnyl, and of these groups especially the saturated groups are preferred.
  • the main idea behind this invention originates from the fact that, at appropriate concentration levels, the time needed for full antimicrobial effect is generally fairly short. In most practical situations the antimicrobial agent is also administered in a very large excess. Therefore, in many applications the toxic compound is active for a long time after it has exerted its antimicrobial action which is both undesirable and unnecessary.
  • the invention discloses a principle, according to which the antimicrobial compound loses its biological activity and toxic action by a hydrolytic reaction.
  • the rate of hydrolysis can be regulated by small changes of pH and electrolyte concentration leading to harmless end-products within the physiologically suitable pH-range from about 6 to about 8.5.
  • solubility of the esters in polar organic solvents is of the order 1 g/ml.
  • Such formulations are highly stable and allow long-term storage.
  • esters are highly active against a brod spectrum of Grampositive and Gramnegative bacteria, as well as fungi, and examples of test data are given below.
  • the temporary disinfecting effect of the esters may be used in hygienic products such as diapers, tampons, masks, napkins, and cosmetic powders. It may also be employed in disinfectants, e.g. for food industry equipment, in bubble baths, swimming pools, and mouthwashes; and for treatment of packages, food industry equipment, food, drinking water etc.
  • the esters can be applied to webs and garments by dipping or spraying a slightly acid, aqueous solution of the esters followed by a rapid drying.
  • Cellulosic fibers may be impregnated by adding the esters to the cellulose pulp slurry in a head-box.
  • the esters When used in dry form, the esters may have the form of a powder or a tablet, for example, an effervescant tablet.
  • the esters II may be prepared by conventional method by a reacting a chloro- or bromoacetyl halide with an alcohol in a halogenated hydrocarbon to an alkyl chloro- or bromoacetate. This ester is then converted into an ester having the formula II by a reaction with gaseous trialkylamine in a solvent such as acetone or toluene.
  • the esters III and IV may be manufactured by direct esterification of the corresponding amino acids with a long chain fatty alcohol using p-toluenesulphonic acid as a catalyst.
  • CTAB cetyltrimethylammonium bromide
  • the effect was measured as the concentration needed for reducing the number of viable bacteria by a factor of 10 5 using E. coli (NCTC 10418) as test organism during 5 minutes contact time. The results are shown in the Table below.
  • esters have an appropriate bactericidal effect.
  • the rate of hydrolysis is also determined dependent. On a temperature increase from 25° C. to 30° C., the half-life at pH 7.0 is decreased from 9 to 5 hrs.
  • the rate of hydrolysis and thereby the duration of the biological activity of the esters can also be regulated according to this invention by the salt concentration of the medium.
  • the rate of hydrolysis is decreased considerably by an increase in sodium chloride concentration.
  • Table below the effect of sodium chloride on hydrolysis of the compound in Example 2 at pH 7.9 and 30° C. is shown.
  • the degree of hydrolysis was determined by analysis of the liberated 1-tetradekanol by gas chromatography (packed 4 ft glass column with 3% SP-2100 on 80/100 Supelcoport; isotermally at 130° C.).
  • the 1-tetradekanol was isolated by careful extraction with hexane. Internal standardization was carried out by means of 1-hexadecanol.
  • Bactericidal effect was determined by dilution of a 1 ml sample to 25 ppm with 5 ml of a sterile buffer followed by addition of 60 ⁇ l of the bacterial suspension. After 5 min at room temperature, a 100-fold dilution and spreading on an agar plate using a Spiral Plater system was performed. The plates were incubated at 37° C. for 20 hrs and counted. Data from the experiments are given in the Table below.
  • the compounds listed below were tested at a 25 ppm level against five different microorganisms in a buffered water solution (10 mM, pH 7.4). One set of solutions was immediately inoculated while the other set was kept at 30° C. for 24 hrs prior to inoculation. The contact time was 5 min.
  • St.a. Staphylococcus aureus NCTC 10788
  • Ps.a. Pseudomonas aeruginosa ATCC 15442
  • C.a. Candica albicans ATCC 10231
  • Lysine-tetradecylester, betaine-tetradecylester, and betaine-hexadecylester were tested at different concentrations for the disinfection of drinking water.
  • the drinking water contained Salmonella typhimurium 395 MS AND Shigella sonnei.
  • Salmonella typhimurium 395 MS AND Shigella sonnei At a concentration of 10 ppm of the microbicide at a pH of about 7 the above mentioned bacteria were completely inactivated within 10 minutes. Complete inactivation means that more than 99.99% of the bacteria were killed.
  • concentrations of 100 ppm were sufficient to cause complete inactivation in 10 minutes.
  • Camphylobacter jejuni was inactivated to the same extent under these conditions.
  • Disinfection of water containing Pseudomonas aeruginosa strain 10783 was carried out by adding betaine-tetradecylester and lysine-tetradecylester.
  • the species Pseudomonas aeruginosa is well known for its resistance against cationic surfactant disinfectants.
  • concentration of the esters of 100 ppm the bacteria were completely inactivated within one minute.
  • the same results were also obtained in the presence of contaminating organic material (0.2% bovine serum albumin).

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Use of a long chain alkyl ester as a temporary microbicide at pH-values from about 6 to about 8.5. The long-chain alkyl ester has the formula ##STR1## where RI, RII, and RIII are hydrogen or lower alkyl groups and RIV is an long chain alkyl group having 10-18 carbon atoms, RV is hydrogen or a group having the formula RVI N+ H3 where RVI is an alkylene group having 3-4 carbon atoms, A is a monovalent counter ion and n is the number of cationic groups in the ester compound. The ester exhibits a temporary microbicidal effect due to a hydrolytic reaction. As a consequence the toxic effect on human and animals cells and tissues will be low.

Description

BACKGROUND OF THE INVENTION
Amphiphilic compounds of the quaternary ammonium type have for a long time been known to exhibit strong antimicrobial activity, the disclosure by Domagk in 1935 having great impact on the development of this field. (G. Domagk, Dtsch. Med. Wochenschr. 61, 829 (1935)). It has become evident, however, from studies of acute as well as chronic toxicity, that these compounds may give rise to skin irritation and hypersensitivity, and therefore are not quite recommendable for certain applications.
SUMMARY OF THE INVENTION
Therefore, it is an object of this invention to find antimicrobial compounds which do not have the drawback mentioned above. Another object of the invention is to permit a rapid inactivation by a controllable degradation of the antimicrobial compound. Still another object is that the degradation will take place at pH-values from about 6 to about 8.5 which is a pH-value that does not give rise to skin irritation and the like.
It has now been foiund that these objects are met by using a long chain alkyl ester having the general formula ##STR2## where RI, RII, and RIII are hydrogen or lower alkyl groups and RIV is an long chain alkyl group having 10-18 carbon atoms, RV is hydrogen or a group having the formula RVI N+ H3 where RVI is an alkylene group having 3-4 carbon atoms, A is a monovalent counter ion and n is the number of cationic groups in the ester compound, as a temporary microbicide in an aqueous medium at a pH-vlue from about 6 to about 8.5 for disinfection of products or in products for disinfection to be brought in contact with food, human beings and animals, e.g. human and animal cells and tissue. In the present invention the microorganisms are inactivated in an initial phase by exposing the microorganisms in an aqueous medium at a pH-value from about 6 to about 8.5 to the long-chain alkyl ester and the long-chain alkyl ester is detoxicated due to a hydrolytic reactiion which takes place concurrently and subsequently with the inactivation of the microorganisms so that the content of the ester in a short time reaches an innocuous level. The lower alkyl groups RI, RII and RIII are preferably alkyl groups having 1-4 carbon atoms and most preferably they are methyl groups. Preferably RIV is a straight chain alkyl group. The counter ion A is normally a halide ion, such as chloride, or HSO4 -. Examples of preferred embodiments are esters having the formulae ##STR3## where RIV and A have the above meanings.
In general, ordinary alkyl ester compounds have an extremely slow hydrolysis rate at these pH-values. The charged long chain alkyl esters I exhibit a useful rate of ester hydrolysis in a pH-range from about 6 to about 8.5 and especially in the pH-range from about 7 to about 8 which, in the present invention, is advantageously used in order to obtain an initially complete microbicidal effect while only a limited toxic effect is exerted against human beings and animals. The latter advantage will be more pronounced when longer contact times, e.g. half an hour or more, are had between the disinfected or disinfecting products and human beings and animals. Normally the long-chain alkyl esters are added in such an amount that the effective concentration in the aqueous medium will be at least 2 ppm, preferably between 5 and 200 ppm, even if other concentrations may be used depending on the specific conditions at application.
Examples of lower alkyl groups in the above formula are methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, and isobutyl, but ethyl and especially methyl are the preferred groups. The long chain alkyl group RIV can be decanyl, dodecanyl, dodecenyl, tetradecanyl, hexadecanyl, octadecanyl, octadecenyl, octadecandienyl, and octadecantrietnyl, and of these groups especially the saturated groups are preferred.
Compounds having the above formula have earlier been disclosed in the chemical literature (I. Metayer, Ann pharm. franc. 10, 435, 439 (1952)) and they have also been found to have antibacterial effects (A. E. Epstein et al., Khim. Farm. Zh. 14, 23 (1980) and Teruaki Nakamiya et al., Ferment. Technol. Vol. 54, No 6, p 369-374, 1976). No reports referring to the loss of biological activity as a result of ester hydrolysis in the pH-region around 7 have been made, and therefore said literature does not indicate any advantages to use these compounds instead of prior known microbicidal compounds.
The main idea behind this invention originates from the fact that, at appropriate concentration levels, the time needed for full antimicrobial effect is generally fairly short. In most practical situations the antimicrobial agent is also administered in a very large excess. Therefore, in many applications the toxic compound is active for a long time after it has exerted its antimicrobial action which is both undesirable and unnecessary. The invention discloses a principle, according to which the antimicrobial compound loses its biological activity and toxic action by a hydrolytic reaction. The rate of hydrolysis can be regulated by small changes of pH and electrolyte concentration leading to harmless end-products within the physiologically suitable pH-range from about 6 to about 8.5.
The solubility of the esters in polar organic solvents, such as lower alcohols and alcohol/water mixtures, is of the order 1 g/ml. Such formulations are highly stable and allow long-term storage.
The esters are highly active against a brod spectrum of Grampositive and Gramnegative bacteria, as well as fungi, and examples of test data are given below.
The temporary disinfecting effect of the esters may be used in hygienic products such as diapers, tampons, masks, napkins, and cosmetic powders. It may also be employed in disinfectants, e.g. for food industry equipment, in bubble baths, swimming pools, and mouthwashes; and for treatment of packages, food industry equipment, food, drinking water etc. The esters can be applied to webs and garments by dipping or spraying a slightly acid, aqueous solution of the esters followed by a rapid drying. Cellulosic fibers may be impregnated by adding the esters to the cellulose pulp slurry in a head-box. When used in dry form, the esters may have the form of a powder or a tablet, for example, an effervescant tablet.
The esters II may be prepared by conventional method by a reacting a chloro- or bromoacetyl halide with an alcohol in a halogenated hydrocarbon to an alkyl chloro- or bromoacetate. This ester is then converted into an ester having the formula II by a reaction with gaseous trialkylamine in a solvent such as acetone or toluene. The esters III and IV may be manufactured by direct esterification of the corresponding amino acids with a long chain fatty alcohol using p-toluenesulphonic acid as a catalyst.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The following examples will further illustrate the invention.
Example 1
The bactericidal effect of three esters having the following formula ##STR4## where p was 10, 12 and 14, respectively, were determined and compared with cetyltrimethylammonium bromide (CTAB), a wellknown bactericide. The effect was measured as the concentration needed for reducing the number of viable bacteria by a factor of 105 using E. coli (NCTC 10418) as test organism during 5 minutes contact time. The results are shown in the Table below.
              TABLE 1                                                     
______________________________________                                    
Compound      Concentration                                               
p             ppm                                                         
______________________________________                                    
10            50                                                          
12            12.5                                                        
14            >100                                                        
CTAB          12.5                                                        
______________________________________
From the result it is evident that the esters have an appropriate bactericidal effect.
Example 2
The activity towards a series of microorganisms was determined for the compound in Example 1 having a total of 14 carbon atoms in its alkyl chain, i.e., p=12, a betaine ester. Relevant test data are given in the Table below. The activity is expressed as log (cfu/ml) at a 12.5 ppm level and a 5 min contact time in phosphate buffered saline at room temperature. Effects are related to a control (without bactericide) and to CTAB. G+ and G- denote Grampositive and Gramnegative species, respectively.
              TABLE 2                                                     
______________________________________                                    
                log (cfu/ml)                                              
                           betaine                                        
Microorganisms (Type)                                                     
                  control  ester    CTAB                                  
______________________________________                                    
Bacillus megaterium (G+)                                                  
                  6.7      <3.3     <3.3                                  
E. coli (G-)      7.0      <3.3     <3.3                                  
Candida albicans (yeast)                                                  
                  6.2      6.2      5.7                                   
Pseudomonas aeruginosa (G-)                                               
                  7.4      7.5      7.5                                   
Staphylococcus aureus (G+)                                                
                  5.8      <3.3     <3.3                                  
Salmonella typhimurium (G-)                                               
                  5.5      3.9      3.8                                   
______________________________________
The effects of the betaine ester and of CTAB are the same within experimental error. Except against the more resistant Ps. aeruginosa and the yeast C. albicans, high activities are found even at these low concentrations.
Example 3
The rate of alkaline hydrolysis of the present esters of betaines was determined for the compound in Example 1 having a total of 14 carbon atoms in its alkyl chain (p=12). The conditions during the test and results obtained are given in the Table below.
              TABLE 3                                                     
______________________________________                                    
Hydrolysis (given in %) at various pH-values and reaction                 
times at 30° C.:                                                   
time   pH                                                                 
hrs    2.6    3        4    5    6   7    8    9                          
______________________________________                                    
0.25                                            96                        
0.5                                       12   100                        
1                                     5   60   100                        
1.5                                       87                              
2                                 2  10                                   
3                                         100                             
4                                    37   100                             
8      <1     <1       1             80                                   
18                               16                                       
20                                   98                                   
24     <1     2        3     5                                            
46                               85                                       
48     <1     2        5    10                                            
120                                                                       
144     1     6        12   22                                            
______________________________________
The rate of hydrolysis is also determined dependent. On a temperature increase from 25° C. to 30° C., the half-life at pH 7.0 is decreased from 9 to 5 hrs.
Example 4
The rate of hydrolysis and thereby the duration of the biological activity of the esters can also be regulated according to this invention by the salt concentration of the medium. The rate of hydrolysis is decreased considerably by an increase in sodium chloride concentration. In the Table below, the effect of sodium chloride on hydrolysis of the compound in Example 2 at pH 7.9 and 30° C. is shown.
              TABLE 4                                                     
______________________________________                                    
Hydrolysis, %                                                             
         Molarity of NaCl                                                 
t, hrs     0      0.1          0.5 1.0                                    
______________________________________                                    
1          51      9            6   2                                     
2          95     56            9   4                                     
5          100    100          28  12                                     
48                             95  77                                     
______________________________________
Example 5
A solution of 150 ppm of the compound in Example 1 in 10 mM phosphate buffer, pH 8.0, was analyzed at different points of time with respect to degree of hydrolysis, as well as bactericidal effect against E. coli (NCTC 10418). The degree of hydrolysis was determined by analysis of the liberated 1-tetradekanol by gas chromatography (packed 4 ft glass column with 3% SP-2100 on 80/100 Supelcoport; isotermally at 130° C.). The 1-tetradekanol was isolated by careful extraction with hexane. Internal standardization was carried out by means of 1-hexadecanol. Bactericidal effect was determined by dilution of a 1 ml sample to 25 ppm with 5 ml of a sterile buffer followed by addition of 60 μl of the bacterial suspension. After 5 min at room temperature, a 100-fold dilution and spreading on an agar plate using a Spiral Plater system was performed. The plates were incubated at 37° C. for 20 hrs and counted. Data from the experiments are given in the Table below.
              TABLE 5                                                     
______________________________________                                    
Hydrolysis and the effect on the bacterial activity.                      
                       Viable counts, cfu/ml                              
Time, min  Hydrolysis, %                                                  
                       (control: 7.1 × 10.sup.6)                    
______________________________________                                    
 5                     0                                                  
 23         3                                                             
 30                    4.1 × 10.sup.3                               
 64        25                                                             
109                    3.0 × 10.sup.6                               
118        55                                                             
149        86                                                             
158                    7.9 × 10.sup.6                               
179        89                                                             
199                    7.8 × 10.sup.6                               
217        100                                                            
238        100                                                            
______________________________________
Example 6
The compounds listed below were tested at a 25 ppm level against five different microorganisms in a buffered water solution (10 mM, pH 7.4). One set of solutions was immediately inoculated while the other set was kept at 30° C. for 24 hrs prior to inoculation. The contact time was 5 min.
The results shown in Table 6 were obtained.
              TABLE 6                                                     
______________________________________                                    
                         Δ log                                      
                                 cfu/ml                                   
Compound   Microorganism 0 hrs   24 hrs                                   
______________________________________                                    
LE 16         E.c.       4.3     3.2                                      
              C.a.       6.1     0.7                                      
ORN 14        E.c.       7.1     0                                        
              St.a.      5.2     0                                        
              S.t.       6.7     0                                        
              Ps.a.      8.2     <3.2                                     
              C.a.       6.1     0                                        
BE 14         E.c.       7.1     0.2                                      
              St.a.      6.5     0.2                                      
              S.t.       6.7     0.1                                      
              Ps.a.      8.2     <3.2                                     
              C.a.       3.3     0                                        
CTAB          E.c.       7.1     7.1                                      
              St.a.      6.5     6.4                                      
              S.t.       6.7     6.5                                      
              Ps.a.      8.2     8.2                                      
              C.a.       6.1     6.0                                      
______________________________________                                    
 ##STR5##                                                                 
 ##STR6##                                                                 
 ##STR7##                                                                 
-   E.c.=E. coli NCTC 10418
St.a.=Staphylococcus aureus NCTC 10788
S.t.=Salmonella typhimurium
Ps.a.=Pseudomonas aeruginosa ATCC 15442
C.a.=Candica albicans ATCC 10231
From the results it is evident that the antimicrobial effects of the different long-chain alkyl esters were of the same magnitude as the effect of cetyltrimetylammonium bromide. After 24 hours in the aqueous solution, the effects diminished considerably for the microbicides of the invention. The esters designated with ORN and BE 14 exhibit especially favourable proerties.
Example 7
Lysine-tetradecylester, betaine-tetradecylester, and betaine-hexadecylester were tested at different concentrations for the disinfection of drinking water. The drinking water contained Salmonella typhimurium 395 MS AND Shigella sonnei. At a concentration of 10 ppm of the microbicide at a pH of about 7 the above mentioned bacteria were completely inactivated within 10 minutes. Complete inactivation means that more than 99.99% of the bacteria were killed. In the presence of contaminating material (0.2% bovine serum albumin) concentrations of 100 ppm were sufficient to cause complete inactivation in 10 minutes. Also Camphylobacter jejuni was inactivated to the same extent under these conditions.
Example 8
Disinfection of water containing Pseudomonas aeruginosa strain 10783 was carried out by adding betaine-tetradecylester and lysine-tetradecylester. The species Pseudomonas aeruginosa is well known for its resistance against cationic surfactant disinfectants. At a concentration of the esters of 100 ppm the bacteria were completely inactivated within one minute. The same results were also obtained in the presence of contaminating organic material (0.2% bovine serum albumin).

Claims (14)

We claim:
1. A process of disinfecting at least one of food, human beings, animals and products to be brought in contact with one of food, human beings, and animals to combat microorganisms, comprising:
exposing the at least one of food, human beings, animals and products to a freshly prepared composition having a pH-value ranging from about 6 to about 8.5 and being comprised of an aqueous medium and a long-chain alkyl ester compound having the formula: ##STR8## where RI, RII, AND RIII are hydrogen or lower alkyl groups, RIV is a long-chain alkyl group having 10-18 carbon atoms, RV is hydrogen or a group having the formula RVI N+ H3, where RVI is an alkylene group having 3-4 carbon atoms, A is a monovalent counter ion and n is a number of cationic groups in the ester compound.
2. The process according to claim 1, wherein the ester compound has the general formula: ##STR9##
3. The process according to claim 1, wherein the ester compound has the general formula: ##STR10##
4. The process according to claim 1, wherein the ester compound has the formula: ##STR11##
5. The process according to claim 1, wherein RIV is a straight chain alkyl group.
6. The process according to claim 1, where the microorganisms combatted are selected from bacteria and fungi.
7. The process according to claim 6, wherein the microorganisms combatted are bacteria and are selected from Gramnegative and Grampositive bacteria.
8. A process of disinfecting at least one of food, human beings, animals and products to be brought in contact with one of food, human beings and animals to combat microorganisms, comprising:
exposing the microorganisms to inactivate the microorganisms in an initial phase to a freshly prepared composition having a pH-value ranging from about 6 to about 8.5 and being comprised of an aqueous medium and a long-chain alkyl ester compound having the formula: ##STR12## where RI, RII, AND RIII are hydrogen or lower alkyl groups, RIV is a long-chain alkyl group having 10-18 carbon atoms, RV is hydrogen or a group having the formula RVI N+ H3, where RVI is an alkylene group having 3-4 carbon atoms, A is a monovalent counter ion and n is a number of cationic groups in the ester compound, and
detoxicating the long-chain alkyl ester compound of the composition due to hydrolytic reaction thereof which takes place concurently with and subsequently to the initial phase and which reduces the ester compound content of the composition to innocuous levels.
9. The process according to claim 8, wherein the ester compound has the general formula: ##STR13##
10. The process according to claim 8, wherein the ester compound has the general formula: ##STR14##
11. The process according to claim 8, wherein the ester compound has the formula: ##STR15##
12. The process according to claim 8, wherein RIV is a straight chain alkyl group.
13. The process according to claim 8, where the microorganisms combatted are selected from bacteria and fungi.
14. The process according to claim 13, wherein the microorganisms combatted are bacteria and are selected from Gramnegative and Grampositive bacteria.
US06/948,261 1986-01-07 1986-12-31 Method for disinfection Expired - Fee Related US4790978A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US07/775,096 US5204060A (en) 1986-01-07 1991-10-11 Method for disinfection

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8600046 1986-01-07
SE8600046A SE453553B (en) 1986-01-07 1986-01-07 APPLICATION OF A LONG-CHAIN ALKYLESTER OF A BETAIN AS A TEMPORARY BACTERICIDE

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US07/212,993 Continuation-In-Part US5080902A (en) 1986-01-07 1988-06-29 Article and a prophylactic composition containing a microbicide

Publications (1)

Publication Number Publication Date
US4790978A true US4790978A (en) 1988-12-13

Family

ID=20363025

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/948,261 Expired - Fee Related US4790978A (en) 1986-01-07 1986-12-31 Method for disinfection

Country Status (8)

Country Link
US (1) US4790978A (en)
EP (1) EP0230698B1 (en)
JP (1) JPS62209001A (en)
DE (1) DE3679538D1 (en)
DK (1) DK169904B1 (en)
FI (1) FI83586C (en)
NO (1) NO161953C (en)
SE (1) SE453553B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991007088A1 (en) * 1989-11-22 1991-05-30 Berol Nobel Ab Microbicidal composition containing a cellulose ether
US5080902A (en) * 1986-01-07 1992-01-14 Berol Kemi Ab Article and a prophylactic composition containing a microbicide
US5204060A (en) * 1986-01-07 1993-04-20 Berol Kemi Ab Method for disinfection
US5314689A (en) * 1988-05-26 1994-05-24 Attilio Bernardini Acyl-carnitine for the treatment and prevention of viral infections
US5656177A (en) * 1993-11-30 1997-08-12 Chemische Fabrik Stockhausen Gmbh Oil-in-water emulsions as substitutes for microbicides (biocides) in water carrying systems
US20050069515A1 (en) * 2003-09-25 2005-03-31 Rivers Gordon T. Process and composition for lower toxicity quaternary ammonium compounds
US20070224249A1 (en) * 2006-03-22 2007-09-27 Kelly Albert R Substantially dry disposable device for creating ready-to-use solutions for cleaning and inhibiting the formation of biofilms on surfaces
US20080138327A1 (en) * 2006-03-22 2008-06-12 Kelly Albert R Substantially dry disposable device for creating ready-to-use solutions for cleaning and inhibiting the formation of biofilms on surfaces
US9909086B2 (en) 2012-06-13 2018-03-06 Marie-Esther Saint Victor Green glycine betaine derivative compounds and compositions containing same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8702674L (en) * 1987-06-29 1988-12-30 Berol Kemi Ab PREVENTIVE AGENTS FOR THE FIGHTING OF VENERICAL DISEASES
DE19851452A1 (en) * 1998-11-09 2000-05-11 Cognis Deutschland Gmbh Use of betaine nests as microbicidal active ingredients

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1061457A (en) * 1964-10-16 1967-03-15 Hoffmann La Roche Novel quaternary ammonium compounds and a process for the manufacture thereof
US4446103A (en) * 1980-01-31 1984-05-01 Research Foundation Of State University Of New York Method of disinfecting water with insoluble disinfectant compositions
US4499077A (en) * 1981-02-03 1985-02-12 Stockel Richard F Anti-microbial compositions and associated methods for preparing the same and for the disinfecting of various objects
US4525346A (en) * 1981-09-28 1985-06-25 Alcon Laboratories, Inc. Aqueous antimicrobial ophthalmic solutions
US4601954A (en) * 1984-03-30 1986-07-22 Servicemaster Industries, Inc. Disinfectant formulation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2258869A2 (en) * 1974-01-24 1975-08-22 Phytoderm Lab Amino acid contg. disinfectant compsns - for topical application, contains quat ammonium salt synergist

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1061457A (en) * 1964-10-16 1967-03-15 Hoffmann La Roche Novel quaternary ammonium compounds and a process for the manufacture thereof
US4446103A (en) * 1980-01-31 1984-05-01 Research Foundation Of State University Of New York Method of disinfecting water with insoluble disinfectant compositions
US4499077A (en) * 1981-02-03 1985-02-12 Stockel Richard F Anti-microbial compositions and associated methods for preparing the same and for the disinfecting of various objects
US4525346A (en) * 1981-09-28 1985-06-25 Alcon Laboratories, Inc. Aqueous antimicrobial ophthalmic solutions
US4601954A (en) * 1984-03-30 1986-07-22 Servicemaster Industries, Inc. Disinfectant formulation

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
A. E. Epsbtein et al., Bactericidial Quaternary Ammonium Salts Derived from Monochloro Acetate Esters, Khim. Farm. Zh. 14, 23 (1980), pp. 292 295. *
A. E. Epsbtein et al., Bactericidial Quaternary Ammonium Salts Derived from Monochloro Acetate Esters, Khim. Farm. Zh. 14, 23 (1980), pp. 292-295.
I M tayer, Ann Pharm. Franc. 10, pp. 435 439, 1952. *
I Metayer, Ann Pharm. Franc. 10, pp. 435-439, 1952.
T. Nakamiya et al., Antibacterial Activity of Lauryl Ester of DL Lysine, Ferment Technology, vol. 54, No. 6, pp. 36 374, 1976. *
T. Nakamiya et al., Antibacterial Activity of Lauryl Ester of DL-Lysine, Ferment Technology, vol. 54, No. 6, pp. 36-374, 1976.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5080902A (en) * 1986-01-07 1992-01-14 Berol Kemi Ab Article and a prophylactic composition containing a microbicide
US5204060A (en) * 1986-01-07 1993-04-20 Berol Kemi Ab Method for disinfection
US5314689A (en) * 1988-05-26 1994-05-24 Attilio Bernardini Acyl-carnitine for the treatment and prevention of viral infections
WO1991007088A1 (en) * 1989-11-22 1991-05-30 Berol Nobel Ab Microbicidal composition containing a cellulose ether
US5656177A (en) * 1993-11-30 1997-08-12 Chemische Fabrik Stockhausen Gmbh Oil-in-water emulsions as substitutes for microbicides (biocides) in water carrying systems
US20050069515A1 (en) * 2003-09-25 2005-03-31 Rivers Gordon T. Process and composition for lower toxicity quaternary ammonium compounds
US7314951B2 (en) 2003-09-25 2008-01-01 Baker Hughes Incorporated Process and composition for lower toxicity quaternary ammonium compounds
US20070224249A1 (en) * 2006-03-22 2007-09-27 Kelly Albert R Substantially dry disposable device for creating ready-to-use solutions for cleaning and inhibiting the formation of biofilms on surfaces
US20080138327A1 (en) * 2006-03-22 2008-06-12 Kelly Albert R Substantially dry disposable device for creating ready-to-use solutions for cleaning and inhibiting the formation of biofilms on surfaces
US9909086B2 (en) 2012-06-13 2018-03-06 Marie-Esther Saint Victor Green glycine betaine derivative compounds and compositions containing same

Also Published As

Publication number Publication date
DK4687A (en) 1987-07-08
SE8600046L (en) 1987-07-08
DK169904B1 (en) 1995-04-03
DK4687D0 (en) 1987-01-06
EP0230698A1 (en) 1987-08-05
FI83586B (en) 1991-04-30
SE8600046D0 (en) 1986-01-07
FI865312A (en) 1987-07-08
NO161953C (en) 1989-10-18
FI83586C (en) 1991-08-12
NO161953B (en) 1989-07-10
SE453553B (en) 1988-02-15
JPS62209001A (en) 1987-09-14
NO870056L (en) 1987-07-08
FI865312A0 (en) 1986-12-29
EP0230698B1 (en) 1991-05-29
DE3679538D1 (en) 1991-07-04
NO870056D0 (en) 1987-01-06

Similar Documents

Publication Publication Date Title
US5204060A (en) Method for disinfection
US4654213A (en) Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2&#39;-dithiobis-pyridine-1,1&#39;-dioxide and a water soluble zinc salt
US5707993A (en) Glycine anhydride dimethylol as a biocide and preservative
US5049440A (en) Wet wiper natural acid and salt preservative composition
US20030195263A1 (en) Use of 1,2-decandiol for combating germs causing body odour
US4790978A (en) Method for disinfection
CA2728327A1 (en) Use of cationic surfactants as sporicidal agents
US5527826A (en) Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid
EP0741518B1 (en) Synergistic antimicrobial compositions containing methylene-bis(thiocyanate) and an organic acid
US5080902A (en) Article and a prophylactic composition containing a microbicide
JPH02134302A (en) Antibacterial composition and its usage
KR0179236B1 (en) Humidifier Detergent Composition Using Natural Extracts
EP0463202B1 (en) Composition and method for sterilizing pathogens in the presence of water
AU745268B2 (en) Synergistic antimicrobial compositions containing dodecylmorpholine or a salt thereof and dodecylamine or salt thereof
EP0034684B1 (en) 1,3-diformyloxy-2-bromo-2-nitropropane, its preparation and use in anti-microbial applications
EP0298065A2 (en) Prophylactic agent for controlling venereal diseases
DD278061A1 (en) MICROBICIDE MEDIUM
US3141819A (en) Dieldrin-pmds compositions for protection of wool
RU2094989C1 (en) Fungicide and bactericide
JPH04275202A (en) Non-toxic enzymatic sterilizing agent
DD278062A1 (en) Bactericides and fungicides
JPH0417161B2 (en)
AU1836099A (en) Synergistic antimicrobial compositions containing methylene-bis(thiocyanate) and an organic acid

Legal Events

Date Code Title Description
AS Assignment

Owner name: BEROL KEMI AB, BOX 851 S-444 01 STENUNGSUND, SWED

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:LINDSTEDT, MAGNUS;EDEBO, LARS;ALLENMARK, STIG;REEL/FRAME:004703/0799

Effective date: 19870112

Owner name: BEROL KEMI AB,SWEDEN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LINDSTEDT, MAGNUS;EDEBO, LARS;ALLENMARK, STIG;REEL/FRAME:004703/0799

Effective date: 19870112

CC Certificate of correction
FPAY Fee payment

Year of fee payment: 4

CC Certificate of correction
REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
FP Lapsed due to failure to pay maintenance fee

Effective date: 19961218

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362